Article
Biochemistry & Molecular Biology
Laura F. Pena, Enol Lopez, Angel Sanchez-Gonzalez, Asuncion Barbero
Summary: A convenient method has been developed for the regioselective synthesis of allyl- and vinylsilyl alcohols from a common precursor by selecting suitable reaction conditions. These alcohols have been used in silyl-Prins cyclizations to prepare disubstituted oxygenated heterocycles in a one-pot sequential reaction. The reaction outcomes are highly dependent on the starting alkenylsilyl alcohol and reaction conditions, with various competitive pathways observed. However, the use of vinylsilyl alcohols has shown promising results in the preparation of differentially substituted cis-2,6-dihydropyrans.
Article
Chemistry, Multidisciplinary
Hai-xuan Liu, Fei Ji, Yu Chen, Ya Gao, Jun-ke Wang, Ming-zhi Zhang, Fang Liu, Qiang Sha
Summary: This study reports a divergent synthesis of a variety of 2 alpha- and 5 alpha-substituted furan derivatives from 2-hydroxy-1,4-diones, achieved through selective reactions using different substrates and catalysts. The products showed moderate antifungal activity against Rhizoctorzia solani and Botrytis cinerea.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Jonathan Trevorrow, Anne O'Kearney-McMullan, Lucie Miller Potucka, Adrian P. Dobbs
Summary: In this study, we report a novel and highly efficient method for the synthesis of hydroxydi- and hydroxytetra-hydropyrans as spiroketal precursors. This method bypasses the challenges associated with traditional multistep syntheses and protecting group manipulation, providing a new pathway for studying the spiroketal moiety.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Sho Amemiya, Shingo Okemoto, Akira Tsubouchi, Akio Saito
Summary: A synthetic method for alpha-(aminoethyl)-alpha,beta-enones from aryl-substituted homopropargyl sulfonamides and aldehydes was developed, representing the first synthesis of conjugated enones via alkyne aza-Prins cyclization. These products could be further converted into pyrrolidines.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Vallabhareddy Satteyyanaidu, Rapelli Chandrashekhar, B. V. Subba Reddy, Claudia Lalli
Summary: This study proposes the synthesis of biologically relevant hexahydro-1H-pyrano[3,4-c]chromenes through a tandem Prins/Friedels-Crafts process catalyzed by BF3.Et2O. The diastereoselectivity of the process is controlled by the geometry of the homoallylic alcohol. Additionally, high yields and good diastereoselectivity of the Prins product can be achieved when the reaction is promoted by AlCl3 as Lewis acid in the presence of an external nucleophile.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Crystallography
Weiqing She, Zhenzhen Xu, Lianjie Zhai, Junlin Zhang, Jie Huang, Weiqiang Pang, Bozhou Wang
Summary: Due to the introduction of oxygen atoms, N-oxide energetic compounds possess unique advantages in terms of oxygen balance, detonation properties, and energy density, which have attracted extensive attention from researchers worldwide. This article provides a comprehensive review of the synthetic strategies for two categories of N-oxides, azine N-oxides and azole N-oxides, and discusses the reaction mechanisms of aromatic N-oxide frameworks and their applications in creating high-energy substances. Furthermore, the energetic properties of N-oxide energetic compounds are compared and summarized.
Article
Chemistry, Multidisciplinary
Christina Jaeger, Mona Haase, Katja Koschorreck, Vlada B. Urlacher, Jan Deska
Summary: Biocatalytic oxidation of acylated hydroxylamines enables selective introduction of nitrogen functionalities by activating allylic C-H bonds. Utilizing laccases or oxidase/peroxidase couple with air as the oxidant, acylnitroso species are generated under mild aqueous conditions. These reactive intermediates undergo C-N bond formation through an ene-type mechanism, providing high yields in both intramolecular and intermolecular enzymatic aminations. Investigations on different pathways and labelling studies provide insight into the promiscuity of oxidoreductases as catalysts for nitroso-based transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Krishnaji Tadiparthi, Allen Roy, Raghavendra Sakirolla, B. V. Subba Reddy, Jhillu Singh Yadav
Summary: This article discusses the research efforts in the past two decades (2005-2020) towards the synthesis of various natural products using Prins cyclization as a key step. The synthetic utility of this reaction has been investigated and successfully demonstrated on various molecules.
Article
Chemistry, Organic
Victoria Sinka, Daniel A. Cruz, Victor S. Martin, Juan I. Padron
Summary: The shortest enantioselective total syntheses of (+)-isolaurepinnacin and (+)-neoisoprelaurefucin were achieved using a common parallel synthetic strategy based on Prins-Peterson cyclization in their core construction. In only one step, a seven-membered ring oxacycle with the correct cis-stereochemistry ring closure and the Δ4 position of the endocyclic double bond in (+)-isolaurepinnacin was obtained. This unsaturation was also necessary to access the bromodioxabicycle in (+)-neoisoprelaurefucin.
Article
Chemistry, Physical
Philip R. D. Murray, Isabelle Nathalie-Marie Leibler, Sandrine M. Hell, Eris Villalona, Abigail G. Doyle, Robert R. Knowles
Summary: We introduce a two-component annulation strategy that involves the combination of aryl alkenes and redox-active radical precursors bearing tethered nucleophiles, enabling the synthesis of a diverse collection of five- and six-membered saturated heterocycles. This strategy employs an Ir(III) photocatalyst and a Bronsted acid under visible-light irradiation. The synthesis involves reductive proton-coupled electron transfer, radical addition to alkene, oxidative radical-polar crossover, and cyclization of the tethered nucleophile. This approach allows the easy access to a wide range of heterocycles, including pyrrolidines, piperidines, tetrahydrofurans, morpholines, delta-valerolactones, and dioxanones. It is amenable to gram-scale preparation and complex fragment coupling.
Article
Biochemistry & Molecular Biology
Fedor E. Teslenko, Leonid L. Fershtat
Summary: An optimized synthetic protocol for the assembly of Kuhn verdazyls was developed based on an azo coupling and base-mediated cyclization. The formation mechanism of Kuhn verdazyls was found to involve the intermediate formation of verdazylium cations, which were in situ reduced to leucoverdazyls and then deprotonated to generate corresponding anions. The synthesized verdazyls were characterized by their spectroscopic and electrochemical behavior. These results provide a reliable basis for further investigation in the chemistry and applications of verdazyls.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Physical
Jian-Shu Wang, Jiangjie Zhang, Siqi Wang, Jun Ying, Chuan-Ying Li, Xiao-Feng Wu
Summary: A novel palladium-catalyzed domino carbonylative cyclization has been developed for the rapid construction of functionalized heterocycles. The reaction proceeds smoothly with the consecutive formation of C-C and C-X bonds using benzene-1,3,5-triyl triformate as the CO source, yielding a variety of biologically relevant derivatives.
JOURNAL OF CATALYSIS
(2022)
Review
Chemistry, Applied
Dimitris Matiadis
Summary: 2-Pyrazolines are important five-membered heterocycles with two adjacent nitrogen atoms. They have various functional groups and unique biological properties, and are used as building blocks. In recent years, there has been significant progress in the synthesis of 2-pyrazolines, with the development of novel strategies and improvements of existing protocols. This review summarizes the synthetic methodologies from 2012 to 2022, discussing the challenges, capabilities, scopes, and limitations of the reactions, as well as substitution patterns and mechanisms where applicable.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Organic
Behnoush Seifinoferest, Arezoo Tanbakouchian, Bagher Larijani, Mohammad Mahdavi
Summary: Carbon-nitrogen bond formation is a crucial tool in drug discovery, with Buchwald-Hartwig and Ullman-Goldberg methods being proven efficient for synthesizing heterocycles. Researchers have been focusing on developing new and faster methods for N-containing heterocycle synthesis.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Efraim Reyes, Liher Prieto, Uxue Uria, Luisa Carrillo, Jose L. Vicario
Summary: The Prins reaction is a convenient method for synthesizing oxygen-containing heterocyclic compounds, especially tetrahydropyrans and tetrahydrofurans. Recent years have seen impressive improvements in its performance and scope, particularly in the development of new catalytic and enantioselective versions.
Review
Biochemistry & Molecular Biology
Amanda J. Price, Steven Howard, Benjamin D. Cons
STRUCTURE-BASED DRUG DESIGN: INSIGHTS FROM ACADEMIA AND INDUSTRY
(2017)
Article
Chemistry, Organic
Benjamin D. Cons, Adam J. Bunt, Christopher D. Bailey, Christine L. Willis
Article
Spectroscopy
Girija S. Singh, Tshepo Pheko
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
(2008)
Article
Spectroscopy
Girija S. Singh, Tshepo Pheko
SPECTROSCOPY LETTERS
(2008)
Article
Chemistry, Medicinal
Gianni Chessari, Ian R. Hardcastle, Jong Sook Ahn, Burcu Anil, Elizabeth Anscombe, Ruth H. Bawn, Luke D. Bevan, Timothy J. Blackburn, Ildiko Buck, Celine Cano, Benoit Carbain, Juan Castro, Ben Cons, Sarah J. Cully, Jane A. Endicott, Lynsey Fazal, Bernard T. Golding, Roger J. Griffin, Karen Haggerty, Suzannah J. Harnor, Keisha Hearn, Stephen Hobson, Rhian S. Holvey, Steven Howard, Claire E. Jennings, Christopher N. Johnson, John Lunec, Duncan C. Miller, David R. Newell, Martin E. M. Noble, Judith Reeks, Charlotte H. Revill, Christiane Riedinger, Jeffrey D. St Denis, Emiliano Tamanini, Huw Thomas, Neil T. Thompson, Mladen Vinkovic, Stephen R. Wedge, Pamela A. Williams, Nicola E. Wilsher, Bian Zhang, Yan Zhao
Summary: In this study, novel isoindolinone-based MDM2 inhibitors were designed with rational structure guidance and showed potent inhibition of MDM2-p53 interaction, leading to cytostasis in an osteosarcoma xenograft model. These findings highlight the potential of targeting MDM2 in cancer therapy.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Benjamin D. Cons, David G. Twigg, Rajendra Kumar, Gianni Chessari
Summary: Optimization of electrostatic complementarity is an important strategy in structure-based drug discovery for improving the affinity of molecules against a specific protein target, and it can lead to improvements in physicochemical properties, in vitro properties, and off-target selectivity by deliberate optimization of protein-ligand electrostatic complementarity or intramolecular electrostatic interactions.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Organic
T Pheko, GS Singh
LETTERS IN ORGANIC CHEMISTRY
(2006)
